At the present time, no existing antibacterial product provides all features deemed advantageous. There is continual development of resistance by bacterial strains. A reduction of allergic reactions and of irritation at the site of injection, and greater biological half-life (i.e., longer in vivo activity) are currently desirable features for antibacterial products.
U.S. Pat. No. 4,128,654 issued to Fugitt et al. on Dec. 5, 1978, discloses, among others, compounds of the formula: ##STR1## where A=RS(O).sub.n ;
X=Cl, Br or F; PA1 R=C.sub.1 -C.sub.3 alkyl; and PA1 n=0, 1 or 2. PA1 X=OR.sub.2 (R.sub.2 =H or various acyl moieties). PA1 an alkoxy radical having one to five carbon atoms; PA1 a halogen atom; PA1 a trifluoromethyl radical, or PA1 a carboxyl radical which may be esterified. PA1 Ar is phenyl, optionally substituted by halo or trifluoromethyl; PA1 n is 0 or 1; and PA1 X is --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, an acetylene group or --CH.sub.2 O--. PA1 R.sub.1 is R.sub.2 SO.sub.2, ##STR8## R.sub.2 is --NR.sub.3 R.sub.4, --N(OR.sub.3)R.sub.4, --N.sub.3, --NHNH.sub.2, --NX.sub.2, --NR.sub.6 X, --NXZ, ##STR9## or --N.dbd.S(O).sub.n R.sub.8 R.sub.9 ; R.sub.3 and R.sub.4 are independently H, alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons; PA1 R.sub.5 is NR.sub.3 R.sub.4 or OR.sub.3 ; PA1 R.sub.6 is alkyl of 1-4 carbons; PA1 R.sub.7 is alkyl of 1-4 carbons, optionally substituted with one or more halogens; PA1 R.sub.8 and R.sub.9 are independently alkyl of 1-4 carbons or, taken together are --(CH.sub.2).sub.p --; PA1 R.sub.10 is H, alkyl of 1-3 carbons, ##STR10## R.sub.11 is alkyl of 1-12 carbons; R.sub.12 is H, alkyl of 1-5 carbons, CH.sub.2 OH or CH.sub.2 SH; PA1 X is Cl, Br or I; PA1 Z is a physiologically acceptable cation; PA1 m is 2 or 3; PA1 n is 0 or 1; and PA1 p is 3, 4 or 5; PA1 and when R.sub.10 is alkyl of 1-3 carbons, R.sub.1 can also be CH.sub.3 S(O).sub.q where q is 0, 1 or 2; PA1 R.sub.1 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms, OH, CN, NR.sub.5 R.sub.6 or CO.sub.2 R.sub.8 ; C.sub.2 -C.sub.4 alkenyl; --NR.sub.9 R.sub.10 ; --N.sub.3 ; ##STR13## --NX.sub.2 ; NR.sub.9 X --.sup.- NXZ.sup.+ ; R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.2 alkyl or, taken together are --(CH.sub.2).sub.9 --; PA1 R.sub.4 is alkyl of 1-4 carbons, optionally substituted with one or more halogens; PA1 R.sub.5 and R.sub.6 are independently H, alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons; PA1 R.sub.7 is --NR.sub.5 R.sub.6, --OR.sub.5 or ##STR14## R.sub.8 is H or alkyl of 1-4 carbons; R.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.8 cycloalkyl; PA1 R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 cycloalkyl, --OR.sub.8 or --NR.sub.11 R.sub.11A ; PA1 R.sub.11 and R.sub.11A are independently H or C.sub.1 -C.sub.4 alkyl, or taken together, are --(CH.sub.2).sub.r --; PA1 X is Cl, Br or I; PA1 Y is H, F, Cl, Br, alkyl of 1-3 carbons, or NO.sub.2, or A and Y taken together can be --O--(CH.sub.2).sub.t O--; PA1 Z is a physiologically acceptable cation; PA1 n is 0, 1 or 2; PA1 p is 0 or 1; PA1 q is 3, 4 or 5; PA1 r is 4 or 5; PA1 t is 1, 2 or 3; PA1 B is --NH.sub.2, ##STR15## or N.sub.3 ; R.sub.12 is H, C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.8 cycloalkyl; PA1 R.sub.13 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms; C.sub.2 -C.sub.4 alkenyl; C.sub.3 -C.sub.4 cycloalkyl; phenyl; --CH.sub.2 OR.sub.15 ; --CH(OR.sub.16)OR.sub.17 ; --CH.sub.2 S(O).sub.v R.sub.14 ; ##STR16## --OR.sub.18 ; --SR.sub.14 ; --CH.sub.2 N.sub.3 ; the aminoalkyl groups derived from .alpha.-amino acids such as glycine, L-alanine, L-cysteine, L-proline, and D-alanine; --NR.sub.19 R.sub.20 ; or C(NH.sub.2)R.sub.21 R.sub.22 ; PA1 R.sub.14 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms; PA1 R.sub.15 is H or C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms; PA1 R.sub.16 and R.sub.17 are independently C.sub.1 -C.sub.4 alkyl or, taken together, are --(CH.sub.2).sub.m --; PA1 R.sub.18 is C.sub.1 -C.sub.4 alkyl or C.sub.7 -C.sub.11 aralkyl; PA1 R.sub.19 and R.sub.20 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.21 and R.sub.22 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl or, taken together, are --(CH.sub.2).sub.s --; PA1 R.sub.23 is H, alkyl of 1-8 carbons optionally substituted with one or more halogens, or cycloalkyl of 3-8 carbons; PA1 R.sub.24 is alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons; PA1 R.sub.25 is alkyl of 1-4 carbons substituted with one or more of --S(O).sub.n R.sub.24, --OR.sub.8, ##STR17## --NR.sub.5 R.sub.6, or alkenyl of 2-5 carbons optionally substituted with CHO; or a pharmaceutically suitable salt thereof; provided that: PA1 (1) when A is CH.sub.3 S--, then B is not ##STR18## (2) when A is CH.sub.3 SO.sub.2 --, then B is not ##STR19## (3) when A is H.sub.2 NSO.sub.2 -- and B is ##STR20## then R.sub.12 is H; (4) when A is --CN, B is not --N.sub.3 ; PA1 (5) when A is (CH.sub.3).sub.2 CH, B is not NHCOCH.sub.2 Cl; PA1 (6) when A is OR.sub.5, then B is not NH.sub.2 ; PA1 (7) when A is F, then B is not NHCO.sub.2 CH.sub.3. PA1 A, substituted in the para position, is --S(O).sub.n R.sub.1, NO.sub.2, ##STR21## --CH(CH.sub.3).sub.2, --CH.sub.2 CH.sub.3, CH.sub.3 CH(OH)--, or --COCH.sub.2 OCOCH.sub.3 ; PA1 R.sub.1 is C.sub.1 -C.sub.2 alkyl optionally substituted with one or more halogen atoms or NR.sub.5 R.sub.6 ; PA1 R.sub.5 is H or CH.sub.3 ; PA1 R.sub.6 is H or CH.sub.3 ; PA1 R.sub.23 is alkyl of 1-3 carbons; and n is 0, 1 or 2 when R.sub.1 is alkyl or substituted alkyl; n is 2 when R.sub.1 is NR.sub.5 R.sub.6 ; or PA1 R.sub.15 is H or C.sub.1 -C.sub.4 alkyl; and PA1 R.sub.18 is C.sub.1 -C.sub.4 alkyl. PA1 R.sub.12 is H, C.sub.1 -C.sub.20 alkyl or C.sub.3 -C.sub.8 cycloalkyl; and PA1 Y is H, F, Cl, Br or NO.sub.2 (preferably H). PA1 Y is as directly above; PA1 R.sub.12 is H, C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.8 cycloalkyl; PA1 R.sub.13 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms; C.sub.2 -C.sub.4 alkenyl; C.sub.3 -C.sub.4 cycloalkyl; phenyl; --CH.sub.2 OR.sub.15 ; --CH(OR.sub.16)OR.sub.17 ; --CH.sub.2 S(O).sub.u R.sub.14 ; ##STR27## --OR.sub.18 ; --SR.sub.14 ; the aminoalkyl groups derived from .alpha.-amino acids such as glycine, L-alanine, L-cysteine, L-proline, and D-alanine; --NR.sub.19 R.sub.20 ; or C(NH.sub.2)R.sub.21 R.sub.22 ; PA1 R.sub.14 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms; PA1 R.sub.15 is H or C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms; PA1 R.sub.16 and R.sub.17 are independently C.sub.1 -C.sub.4 alkyl or, taken together, are --(CH.sub.2).sub.m --; PA1 R.sub.18 is C.sub.1 -C.sub.4 alkyl or C.sub.7 -C.sub.11 aralkyl; PA1 R.sub.19 and R.sub.20 are independently H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.21 and R.sub.22 are independently H, C.sub.1 -C.sub.2 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl or, taken together, are --(CH.sub.2).sub.s --; PA1 R.sub.1 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms, OH, CN, NR.sub.5 R.sub.6 PA1 CO.sub.2 R.sub.8 ; C.sub.2 -C.sub.4 alkenyl; --NR.sub.9 R.sub.10 ; --N.sub.3 ; ##STR30## --NX.sub.2 ; NR.sub.9 X --.sup.- NXZ.sup.+ ; R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.2 alkyl or, taken together are --(CH.sub.2).sub.q --; PA1 R.sub.4 is alkyl of 1-4 carbons, optionally substituted with one or more halogens; PA1 R.sub.5 and R.sub.6 are independently H, alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons; PA1 R.sub.7 is --NR.sub.5 R.sub.6, --OR.sub.5 or ##STR31## R.sub.8 is H or alkyl of 1-4 carbons; R.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.8 cycloalkyl; PA1 R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 cycloalkyl, --OR.sub.8 or --NR.sub.11 R.sub.11A ; PA1 R.sub.11 and R.sub.11A are independently H or C.sub.1 -C.sub.4 alkyl, or taken together, are --(CH.sub.2).sub.r --; PA1 X is Cl, Br or I; PA1 Y is H, F, Cl, Br, alkyl of 1-3 carbons, or NO.sub.2, or A and Y taken together can be --O--(CH.sub.2).sub.t O--; PA1 Z is a physiologically acceptable cation; PA1 n is 0, 1 or 2; PA1 p is 0 or 1; PA1 q is 3, 4 or 5; PA1 r is 4 or 5; PA1 t is 1, 2 or 3; PA1 B is --NH.sub.2, ##STR32## or N.sub.3 ; R.sub.12 is H, C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.8 cycloalkyl; PA1 R.sub.13 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms; PA1 R.sub.14 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms; PA1 R.sub.15 is H or C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogen atoms; PA1 R.sub.16 and R.sub.17 are independently C.sub.1 -C.sub.4 alkyl or, taken together, are --(CH.sub.2).sub.m --; PA1 R.sub.18 is C.sub.1 -C.sub.4 alkyl or C.sub.7 -C.sub.11 aralkyl; PA1 R.sub.19 and R.sub.20 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.21 and R.sub.22 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl or, taken together, are --(CH.sub.2).sub.s --; PA1 R.sub.23 is H, alkyl of 1-8 carbons optionally substituted with one or more halogens, or cycloalkyl of 3-8 carbons; PA1 R.sub.24 is alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons; PA1 R.sub.25 is alkyl of 1-4 carbons substituted with one or more of --S(O).sub.n R.sub.24, --OR.sub.8, ##STR34## --NR.sub.5 R.sub.6, or alkenyl of 2-5 carbons optionally substituted with CHO; or a pharmaceutically suitable salt thereof; provided that: PA1 (1) when A is CH.sub.3 S--, then B is not ##STR35## (2) when A is CH.sub.3 SO.sub.2 --, then B is not ##STR36## (3) when A is H.sub.2 NSO.sub.2 -- and B is ##STR37## then R.sub.12 is H; (4) when A is --CN, B is not --N.sub.3 ; PA1 (5) when A is (CH.sub.3).sub.2 CH, B is not NHCOCH.sub.2 Cl; PA1 (6) when A is F, then B is not NHCO.sub.2 CH.sub.3.
The compounds are disclosed as being useful in controlling fungal and bacterial diseases of plants.
U.S. Pat. No. Re. 29,607 reissued Apr. 11, 1978 discloses derivatives of 5-hydroxymethyl-3-substituted-2-oxazolidinones of the formula: ##STR2## where R is H, F, CH.sub.3, or CF.sub.3. Such compounds are described as having antidepressive, tranquilizing, sedative, and antiinflammatory properties.
U.S. Pat. No. 4,250,318, which was issued on Feb. 10, 1981, discloses antidepressant compounds of the formula: ##STR3## where R' can be, among others, a para-n-pentylamino group, an SR.sub.1 group where R.sub.1 is C.sub.1 -C.sub.5 alkyl, or an acetylmethylthio group.
U.S. Pat. No. 4,340,606, issued to Fugitt et al. on July 20, 1982, discloses antibacterial agents of the general formula: ##STR4## where R.sub.1 =CH.sub.3, C.sub.2 H.sub.5, CF.sub.2 H, CF.sub.3 or CF.sub.2 CF.sub.2 H; and
U.S. Pat. No. 3,687,965, issued to Fauran et al. on August 29, 1972, discloses compounds of the formula: ##STR5## where
--N(R.sub.1)(R.sub.2) represents either dialkylamino radical in which the alkyl portions have one to five carbon atoms, or a heterocyclic amino radical which may be substituted by an alkyl radical having one to five carbon atoms or by a pyrrolidinocarbonylmethyl radical, and
R.sub.3 represents a phenyl radical which may be substituted by one or more of the following radicals:
The patent states that these compounds possess hypotensive, vasodilatatory, spasmolytic, sedative, myorelaxant, analgesic and antiinflammatory properties. There is no mention of antibacterial properties.
Belgian Pat. No. 892,270, published Aug. 25, 1982, discloses monoamine oxidase inhibitors of the formula ##STR6## where R is H, C.sub.1 -C.sub.4 alkyl or propargyl;
U.S. Pat. No. 4,461,773 issued to W. A. Gregory on July 24, 1984, a continuation-in-part of U.S. patent application No. 417,569 filed Sept. 15, 1982 discloses antibacterial agents of the formula ##STR7## wherein, for the l, and mixtures of the d and l stereoisomers of the compound,
or a pharmaceutically acceptable salt thereof.
None of the cited references nor any known references suggest the novel antibacterial compounds of this invention.